CA2276445C - Transdermal hormone-delivering therapeutic system - Google Patents
Transdermal hormone-delivering therapeutic system Download PDFInfo
- Publication number
- CA2276445C CA2276445C CA002276445A CA2276445A CA2276445C CA 2276445 C CA2276445 C CA 2276445C CA 002276445 A CA002276445 A CA 002276445A CA 2276445 A CA2276445 A CA 2276445A CA 2276445 C CA2276445 C CA 2276445C
- Authority
- CA
- Canada
- Prior art keywords
- weight
- active compound
- patch according
- contact adhesive
- plasticizer
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7046—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds
- A61K9/7069—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising macromolecular compounds obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. polysiloxane, polyesters, polyurethane, polyethylene oxide
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/57—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of two carbon atoms, e.g. pregnane or progesterone
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/70—Web, sheet or filament bases ; Films; Fibres of the matrix type containing drug
- A61K9/7023—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms
- A61K9/703—Transdermal patches and similar drug-containing composite devices, e.g. cataplasms characterised by shape or structure; Details concerning release liner or backing; Refillable patches; User-activated patches
- A61K9/7038—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer
- A61K9/7076—Transdermal patches of the drug-in-adhesive type, i.e. comprising drug in the skin-adhesive layer the adhesive comprising ingredients of undetermined constitution or reaction products thereof, e.g. rosin or other plant resins
Landscapes
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Botany (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
An active compound-containing patch for the controlled delivery of oestradiol or its pharmaceutically acceptable derivatives, alone or in combination with gestagens, to human or animal skin, having an active compound-containing reservoir based on contact adhesives comprising ethylcellulose and tackifying resins is characterized by a contact adhesive having a high plasticizer content.
Description
Transdermal Hormone-Delivering Therapeutic System The invention relates to an active compound-containing patch for the controlled delivery of oestradiol or its pharmaceutically acceptable derivatives, alone or in combination with gestagens, to human or animal skin, having an active compound-containing reservoir based on contact adhesives comprising ethylcellulose and tackifying resins.
Transdermal therapeutic systems have been known for a relatively long time, in particular also for the transdermal administration of hormones, especially oestrogens, if appropriate in combination with gestagens.
The active compounds are provided for this in an active compound reservoir based on contact adhesives, whose adhesiveness must guarantee adequate skin contact on application without excessive softening and without skin irritation occurring, and whose absorption and release of active compound must conform to the desired continuous systemic supply of active compound through the skin.
As a basis for reservoir layers comprising oestradiol, inter alia, different materials based on rubber or polyacrylate, is particular comprising ethanol, have already been proposed (e.g. DE-A-32 05 258 and EP-0 275 716).
DE-A-39 33 460 describes active compound patches based on homo- and copolymers comprising at least one derivative of acrylic or methacrylic acid, which are additionally intended to contain water-swellable substances.
DE-B 40 20 144 discloses a transdermal system, optionally also containing hormone, comprising at least one self-adhesive active compound layer, which besides polyacrylate and a film-forming agent compatible therewith should contain a wide quantitative range of plasticizing active compounds and auxiliaries.
A recently described transdermal therapeutic system (see DE-A 195 00 662) comprises an active compound reservoir, containing an oestradiol and, if appropriate, gestagens, based on ethylcellulose having a high proportion of esters of optionally hydrogenated colophony as a tackifying resin together with up to 20% by weight of lauric acid, which is intended to counteract recrystallization of the active compound and thus a decrease in its release rate.
Surprisingly, it has now been found that an unexpectedly high active compound release of oestradiol and in particular norethindrone acetate can be achieved from an active compound reservoir based on ethylcellulose and tackifying resin which is provided with an unusually high proportion of plasticizer.
The patch according to the invention of the type mentioned at the outset is accordingly characterized in that the contact adhesive contains a high proportion of plasticizer.
In particular, the contact adhesive contains at least 15%
by weight, preferably at least 20% by weight, of plasticizer.
The active compound-containing patch can otherwise contain emulsifiers, antioxidants and absorption enhancers.
Such a patch can be employed, in particular, for a high combined release of both oestradiol and norethindrone acetate.
Transdermal therapeutic systems have been known for a relatively long time, in particular also for the transdermal administration of hormones, especially oestrogens, if appropriate in combination with gestagens.
The active compounds are provided for this in an active compound reservoir based on contact adhesives, whose adhesiveness must guarantee adequate skin contact on application without excessive softening and without skin irritation occurring, and whose absorption and release of active compound must conform to the desired continuous systemic supply of active compound through the skin.
As a basis for reservoir layers comprising oestradiol, inter alia, different materials based on rubber or polyacrylate, is particular comprising ethanol, have already been proposed (e.g. DE-A-32 05 258 and EP-0 275 716).
DE-A-39 33 460 describes active compound patches based on homo- and copolymers comprising at least one derivative of acrylic or methacrylic acid, which are additionally intended to contain water-swellable substances.
DE-B 40 20 144 discloses a transdermal system, optionally also containing hormone, comprising at least one self-adhesive active compound layer, which besides polyacrylate and a film-forming agent compatible therewith should contain a wide quantitative range of plasticizing active compounds and auxiliaries.
A recently described transdermal therapeutic system (see DE-A 195 00 662) comprises an active compound reservoir, containing an oestradiol and, if appropriate, gestagens, based on ethylcellulose having a high proportion of esters of optionally hydrogenated colophony as a tackifying resin together with up to 20% by weight of lauric acid, which is intended to counteract recrystallization of the active compound and thus a decrease in its release rate.
Surprisingly, it has now been found that an unexpectedly high active compound release of oestradiol and in particular norethindrone acetate can be achieved from an active compound reservoir based on ethylcellulose and tackifying resin which is provided with an unusually high proportion of plasticizer.
The patch according to the invention of the type mentioned at the outset is accordingly characterized in that the contact adhesive contains a high proportion of plasticizer.
In particular, the contact adhesive contains at least 15%
by weight, preferably at least 20% by weight, of plasticizer.
The active compound-containing patch can otherwise contain emulsifiers, antioxidants and absorption enhancers.
Such a patch can be employed, in particular, for a high combined release of both oestradiol and norethindrone acetate.
Preferred formulations of such hormone-containing contact adhesive materials according to the invention have the following composition (in % by weight):
Ethylcellulose 5-25%
Tackifying resins 10-70%
Plasticizer/emulsifiers 20-40%
Oestradiol 1-10°~
Norethindrone acetate and/or other gestagens 1-15°~
Although the addition of plasticizers to active compound-containing contact adhesive materials is known per se, such as, for example, also according to the said DE-A
40 20 244, addition of plasticizer to the customary contact adhesives based on polyacrylates, block copolymers and polyisobutylenes is only possible to a limited extent, since from a certain concentration the cohesion of the contact adhesives decreases and they thus become unsuitable for transdermal application.
The fact that just materials based on ethylcellulose/adhesive resin with unusually high additions of plasticizer would afford particularly useful transdermal therapeutic systems with increased skin penetration of the hormones and a particularly low recrystallization tendency thereof together with good wearing properties of the TTS was in no way to be foreseen, as the said, only recently disclosed TTS
development having an active compound reservoir based on ethylcellulose/adhesive resin shows, which as an additive contains lauric acid and not - as now - high proportions of plasticizer.
Ethylcellulose 5-25%
Tackifying resins 10-70%
Plasticizer/emulsifiers 20-40%
Oestradiol 1-10°~
Norethindrone acetate and/or other gestagens 1-15°~
Although the addition of plasticizers to active compound-containing contact adhesive materials is known per se, such as, for example, also according to the said DE-A
40 20 244, addition of plasticizer to the customary contact adhesives based on polyacrylates, block copolymers and polyisobutylenes is only possible to a limited extent, since from a certain concentration the cohesion of the contact adhesives decreases and they thus become unsuitable for transdermal application.
The fact that just materials based on ethylcellulose/adhesive resin with unusually high additions of plasticizer would afford particularly useful transdermal therapeutic systems with increased skin penetration of the hormones and a particularly low recrystallization tendency thereof together with good wearing properties of the TTS was in no way to be foreseen, as the said, only recently disclosed TTS
development having an active compound reservoir based on ethylcellulose/adhesive resin shows, which as an additive contains lauric acid and not - as now - high proportions of plasticizer.
The composition according to the invention of the active compound reservoir based on ethylcellulose/adhesive resin with a high proportion of plasticizer, but without lauric acid, shows a markedly increased release of hormone compared with the materials according to DE-A 195 00 662, in particular on incorporation of a combination of oestradiol and norethindrone acetate.
This is illustrated by the results given below (Tables 1 and 2), of which Table 1 shows the composition of the investigated materials and Table 2 the results of series of tests on the release of active compound.
It is to be seen that by means of the plasticizer content according to the invention a clear improvement in the release and penetration of active compound is achieved.
This is illustrated by the results given below (Tables 1 and 2), of which Table 1 shows the composition of the investigated materials and Table 2 the results of series of tests on the release of active compound.
It is to be seen that by means of the plasticizer content according to the invention a clear improvement in the release and penetration of active compound is achieved.
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Claims (7)
1. Active compound-containing patch for the controlled delivery of oestradiol or its pharmaceutically acceptable derivatives, alone or in combination with gestagens, to human or animal skin, having an active compound-containing reservoir based on contact adhesives comprising ethylcellulose and tackifying resins, characterized by a contact adhesive having a proportion of plasticizer of at least 15% by weight.
2. The patch according to Claim 1, characterized by -a proportion of plasticizer of 20-40% by weight.
3. The patch according to claim 1 or 2, wherein the tackifying resins comprise esters of optionally hydrogenated colophony.
4. The patch according to one of claims 1 to 3, characterized by an emulsifier content in the contact adhesive of at least 15% by weight.
5. The patch according to one of claims 1 to 4, characterized by the following composition of the active compound-containing contact adhesive:
5-25% by weight of ethylcellulose 10-70% by weight of tackifying resins 20-40% by weight of plasticizer/emulsifiers 1-10% by weight of oestradiol content 1-15% by weight of norethindrone acetate and/or other gestagens.
5-25% by weight of ethylcellulose 10-70% by weight of tackifying resins 20-40% by weight of plasticizer/emulsifiers 1-10% by weight of oestradiol content 1-15% by weight of norethindrone acetate and/or other gestagens.
6. The patch according to one of claims 1 to 5, characterized by a content of antioxidants and/or absorption enhancers in the contact adhesive.
7. The patch according to claim 4, characterized by an emulsifier content in the contact adhesive of at least 20% by weight.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19700913.1 | 1997-01-14 | ||
| DE19700913A DE19700913C2 (en) | 1997-01-14 | 1997-01-14 | Transdermal therapeutic system for the delivery of hormones |
| PCT/EP1998/000014 WO1998031349A1 (en) | 1997-01-14 | 1998-01-03 | Transdermal, hormone-delivering therapeutic system |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2276445A1 CA2276445A1 (en) | 1998-07-23 |
| CA2276445C true CA2276445C (en) | 2005-08-09 |
Family
ID=7817287
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002276445A Expired - Fee Related CA2276445C (en) | 1997-01-14 | 1998-01-03 | Transdermal hormone-delivering therapeutic system |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US6274165B1 (en) |
| EP (1) | EP1007014B1 (en) |
| JP (1) | JP3821855B2 (en) |
| KR (1) | KR100561255B1 (en) |
| AT (1) | ATE238778T1 (en) |
| AU (1) | AU729494B2 (en) |
| CA (1) | CA2276445C (en) |
| DE (2) | DE19700913C2 (en) |
| ES (1) | ES2201434T3 (en) |
| NO (1) | NO993385L (en) |
| WO (1) | WO1998031349A1 (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19830651A1 (en) * | 1998-07-09 | 2000-01-13 | Lohmann Therapie Syst Lts | Plaster containing steroids, process for its production and use |
| HU228822B1 (en) * | 1999-11-29 | 2013-05-28 | Lohmann Therapie Syst Lts | Transdermal therapeutic systems with improved stability and a method for the production thereof |
| DE10054713C2 (en) * | 1999-11-29 | 2002-07-18 | Lohmann Therapie Syst Lts | Transdermal therapeutic systems with improved stability and a method for their production |
| WO2001052823A2 (en) | 2000-01-20 | 2001-07-26 | Noven Pharmaceuticals, Inc. | Compositions to effect the release profile in the transdermal administration of drugs |
| DE10025970C2 (en) * | 2000-05-25 | 2002-04-25 | Lohmann Therapie Syst Lts | Estrogen-containing plaster with an active substance reservoir based on ethyl cellulose and an ethylene-vinyl acetate-vinyl pyrrolidone copolymer and its use |
| EP2409690B1 (en) * | 2003-09-29 | 2022-11-09 | Novo Nordisk Health Care AG | Improved stability of progestogen formulations |
| HU227970B1 (en) | 2007-07-10 | 2012-07-30 | Egis Gyogyszergyar Nyrt | Pharmaceutical compositions containing silicones of high volatility |
| CA2854164C (en) * | 2011-11-04 | 2021-04-13 | Agile Therapeutics, Inc. | Dermal delivery compositions and methods |
| US9301920B2 (en) | 2012-06-18 | 2016-04-05 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| EP2782584B1 (en) | 2011-11-23 | 2021-06-09 | TherapeuticsMD, Inc. | Natural combination hormone replacement formulations and therapies |
| MX367596B (en) * | 2012-01-26 | 2019-08-27 | Therapeuticsmd Inc | Transdermal hormone replacement therapies. |
| US10806740B2 (en) | 2012-06-18 | 2020-10-20 | Therapeuticsmd, Inc. | Natural combination hormone replacement formulations and therapies |
| US10806697B2 (en) | 2012-12-21 | 2020-10-20 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US20150196640A1 (en) | 2012-06-18 | 2015-07-16 | Therapeuticsmd, Inc. | Progesterone formulations having a desirable pk profile |
| US20130338122A1 (en) | 2012-06-18 | 2013-12-19 | Therapeuticsmd, Inc. | Transdermal hormone replacement therapies |
| US11154535B2 (en) | 2012-07-31 | 2021-10-26 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| US10045935B2 (en) | 2012-07-31 | 2018-08-14 | Egis Pharmaceuticals Plc | Transdermal formulation containing COX inhibitors |
| US11246875B2 (en) | 2012-12-21 | 2022-02-15 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US11266661B2 (en) | 2012-12-21 | 2022-03-08 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10471072B2 (en) | 2012-12-21 | 2019-11-12 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US9180091B2 (en) | 2012-12-21 | 2015-11-10 | Therapeuticsmd, Inc. | Soluble estradiol capsule for vaginal insertion |
| US10537581B2 (en) | 2012-12-21 | 2020-01-21 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| US10568891B2 (en) | 2012-12-21 | 2020-02-25 | Therapeuticsmd, Inc. | Vaginal inserted estradiol pharmaceutical compositions and methods |
| JP2017516768A (en) | 2014-05-22 | 2017-06-22 | セラピューティックスエムディー インコーポレーテッドＴｈｅｒａｐｅｕｔｉｃｓｍｄ， Ｉｎｃ． | Natural combination hormone replacement therapy and therapy |
| US10328087B2 (en) | 2015-07-23 | 2019-06-25 | Therapeuticsmd, Inc. | Formulations for solubilizing hormones |
| MX2018011705A (en) | 2016-04-01 | 2019-06-10 | Therapeuticsmd Inc | Steroid hormone pharmaceutical composition. |
| WO2017173044A1 (en) | 2016-04-01 | 2017-10-05 | Therapeuticsmd Inc. | Steroid hormone compositions in medium chain oils |
| US11633405B2 (en) | 2020-02-07 | 2023-04-25 | Therapeuticsmd, Inc. | Steroid hormone pharmaceutical formulations |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4291014A (en) * | 1979-01-11 | 1981-09-22 | Key Pharmaceuticals, Inc. | Polymeric diffusion matrix containing estradiol diacetate |
| US4291015A (en) * | 1979-08-14 | 1981-09-22 | Key Pharmaceuticals, Inc. | Polymeric diffusion matrix containing a vasodilator |
| US4379454A (en) * | 1981-02-17 | 1983-04-12 | Alza Corporation | Dosage for coadministering drug and percutaneous absorption enhancer |
| US4906169A (en) * | 1986-12-29 | 1990-03-06 | Rutgers, The State University Of New Jersey | Transdermal estrogen/progestin dosage unit, system and process |
| CN1021196C (en) | 1986-12-29 | 1993-06-16 | 新泽西州州立大学(鲁杰斯) | Prepn. method of progestin unit and system |
| DE3743945A1 (en) * | 1987-09-01 | 1989-03-09 | Lohmann Gmbh & Co Kg | DEVICE FOR DELIVERING SUBSTANCES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| US4994267A (en) * | 1988-03-04 | 1991-02-19 | Noven Pharmaceuticals, Inc. | Transdermal acrylic multipolymer drug delivery system |
| DE3933460A1 (en) | 1989-10-06 | 1991-04-18 | Lohmann Therapie Syst Lts | OSTROGEN-ACTIVE PLASTER |
| DE4020144A1 (en) * | 1990-06-25 | 1992-01-09 | Lohmann Therapie Syst Lts | Patches for topical or transdermal drug delivery - with adhesive layer contg. polyacrylate adhesive and film former |
| US5158734A (en) * | 1991-02-27 | 1992-10-27 | Minnesota Mining And Manufacturing Company | Biomedical electrical connector using a socket receptacle having a resilient sheath |
| DE4230588C1 (en) * | 1992-09-12 | 1993-10-07 | Lohmann Therapie Syst Lts | Dexpanthenol-containing plaster for the transdermal application of steroid hormones and process for its production |
| DE4333595A1 (en) * | 1993-10-01 | 1995-04-06 | Labtec Gmbh | Transdermal therapeutic system for applying drugs to the skin |
| FR2717689B1 (en) * | 1994-03-28 | 1996-07-05 | Lhd Lab Hygiene Dietetique | Transdermal matrix system for the administration of an estrogen and / or a progestin based on a styrene-isoprene-styrene copolymer. |
| FR2717688B1 (en) * | 1994-03-28 | 1996-07-05 | Lhd Lab Hygiene Dietetique | Transdermal matrix system for administration of an estrogen and / or an EVA-based progestin. |
| KR100209469B1 (en) * | 1994-10-05 | 1999-07-15 | 나까도미 히로다카 | Medicinal adjuvants consisting of an n-substituted-o-toluidine derivative and percutaneously absorbable preparations comprising the same |
| DE19500662C2 (en) * | 1995-01-12 | 2001-04-26 | Lohmann Therapie Syst Lts | Plaster containing estradiol and its use |
-
1997
- 1997-01-14 DE DE19700913A patent/DE19700913C2/en not_active Expired - Fee Related
-
1998
- 1998-01-03 EP EP98901337A patent/EP1007014B1/en not_active Expired - Lifetime
- 1998-01-03 JP JP53137798A patent/JP3821855B2/en not_active Expired - Fee Related
- 1998-01-03 ES ES98901337T patent/ES2201434T3/en not_active Expired - Lifetime
- 1998-01-03 DE DE59808186T patent/DE59808186D1/en not_active Expired - Lifetime
- 1998-01-03 US US09/341,212 patent/US6274165B1/en not_active Expired - Fee Related
- 1998-01-03 KR KR1019997006404A patent/KR100561255B1/en not_active IP Right Cessation
- 1998-01-03 WO PCT/EP1998/000014 patent/WO1998031349A1/en not_active Application Discontinuation
- 1998-01-03 AU AU57654/98A patent/AU729494B2/en not_active Ceased
- 1998-01-03 AT AT98901337T patent/ATE238778T1/en not_active IP Right Cessation
- 1998-01-03 CA CA002276445A patent/CA2276445C/en not_active Expired - Fee Related
-
1999
- 1999-07-08 NO NO993385A patent/NO993385L/en not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| CA2276445A1 (en) | 1998-07-23 |
| NO993385D0 (en) | 1999-07-08 |
| JP3821855B2 (en) | 2006-09-13 |
| NO993385L (en) | 1999-07-08 |
| EP1007014B1 (en) | 2003-05-02 |
| DE19700913A1 (en) | 1998-07-16 |
| ES2201434T3 (en) | 2004-03-16 |
| DE59808186D1 (en) | 2003-06-05 |
| AU729494B2 (en) | 2001-02-01 |
| DE19700913C2 (en) | 2001-01-04 |
| US6274165B1 (en) | 2001-08-14 |
| WO1998031349A1 (en) | 1998-07-23 |
| KR100561255B1 (en) | 2006-03-15 |
| KR20000070178A (en) | 2000-11-25 |
| AU5765498A (en) | 1998-08-07 |
| EP1007014A1 (en) | 2000-06-14 |
| ATE238778T1 (en) | 2003-05-15 |
| JP2001508070A (en) | 2001-06-19 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20140103 |